Hydrochloric Acid → 6-chloro-5-methyl-N-phenylpyrimidin-4-amine

HRID 241004

反応式

HRID 241004 の反応式
Cl[C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)(C)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH3:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8188604,6-Dichloro-5-methylpyrimidine

生成物 1

HCID 637349086-chloro-5-methyl-N-phenylpyrimidin-4-amine収率 85.1%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

To a mixture of 4,6-dichloro-5-methylpyrimidine (2.27 g, 13.9 mmol) and aniline (1.0 g, 10.7 mmol) in isopropanol (15 mL) was added concentrated aqueous hydrochloric acid (1.5 mL) and heated to reflux for 2.5 h. The mixture was then concentrated and the residue triturated with ethyl acetate:isopropanol 4:1. The solid was collected by filtration and washed with additional ethyl acetate:isopropanol 4:1 then dried to give 6-chloro-5-methyl-N-phenylpyrimidin-4-amine (2.0 g, 67% yield). 1H NMR (400 MHz, d6-DMSO): 8.85 (s, 1H), 8.26 (s, 1H), 7.60 (d, 2H), 7.35 (tr, 2H), 7.11 (tr, 1H), 2.31 (s, 3H). MS (EI) for C11H10ClN3: 220 (MH+).

後処理

  1. temperatureheated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was then concentrated
  4. customthe residue triturated with ethyl acetate:isopropanol 4:1
  5. filtrationThe solid was collected by filtration
  6. washwashed with additional ethyl acetate:isopropanol 4:1
  7. customthen dried

出典と根拠

ORDレコード
ord-22761ad4d6464744adf8f3738e887d43
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

関連ノート

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